U.S. Pat. No. 2,818,362 (American Cyanamid Co.) describes the synthesis of a new vinyl monomer, N-vinyl-2-oxazolidinone. Polymerization products made from the new monomer are also described. The polymers have been used in molding compositions or as adhesives in the production of optical devices.
U.S. Pat. No. 2,905,690 (The Dow Chemical Company) describes the synthesis of N-vinyl-X-alkyl oxazolidinone compounds using high temperature and high pressure process (Autoclave). It also describes the polymerization of these materials to produce homopolymers and copolymers using various comonomers. The use of the materials is reported as being in the dyestuffs for textiles industry.
U.S. Pat. No. 3,268,485 (The Dow Chemical Company) describes the preparation of homopolymers and copolymers of 3-(2-hydroxyethyl)-5-methyl-2-oxazolidinone acrylates/methacrylates using azo or peroxy initiators.
U.S. Pat. No. 4,639,472 (The Dow Chemical Company) describes the use of N-vinyl oxazolidinones as reactive diluents in radiation curable coatings. The coatings produced are highly oxygen permeable, have good cure properties and have good physical and resistance properties.
U.S. Pat. No. 4,933,462 (The Dow Chemical Company) describes the synthesis of 3-(2-hydroxyethyl)-2-oxazolidinones using a novel anhydrous, catalyst free process to produce highly pure products in high yield.
C. Decker and K. Moussa, Makromol. Chem., 189, 2381-2394 (1988) describes a method based on IR Spectroscopy which has been developed to follow real-time photopolymerizations. The method has been used to look at photoinitiator efficiency, monomer reactivity, light intensity, film thickness and the oxygen inhibition. Various acrylate functional materials have been investigated as reactive acrylate diluents in a photopolymerisable resin and the dependence of the rate of polymerisation and the ultimate degree of conversation on the type of diluents monomer studied. A new monoacrylate oxazolidinone functional material, Acticryl CL 959 (N-(2-acrylyloxyethyl acrylate), developed by SNPE was found to be the most efficient reactive acrylate diluents of those tested.
C. Decker and Khalil Moussa, Journal of Coatings Technology, 65(819), 49-57 (1993) describes the efficiency of newly developed photoinitiators and acrylic monomers by using Real Time Spectroscopy techniques to follow the kinetic profiles of various photopolymerizations. Some of the new monomers are described as being highly reactive leading to remarkable mechanical properties such as hardness, scratch resistance, flexibility and impact resistance. The monomer N-(2-acrylyloxyethyl) oxazolidinone (Acticryl CL-959 (SNPE)) has been reported here as being one of these highly reactive materials.
Lewis acid-catalyzed Michael addition reactions of N-Boc-2-silyloxypyrroles to 3-actyloyl-2-oxazolidinone, Suga, Hiroyuki; Takemoto, Haruka; Kakehi, Akikazu, Heterocycles (2007), 71(2), 361-371 describes the Lewis acid-catalyzed Michael addition of siloxypyrroles to acryloyloxazolidinone. A slow addition of the 2-silyloxypyrrole at −25° C. was needed to obtain good yields (77-80%).
Known compounds comprising an oxazolidinone ring compounds include:    CAS Registry Number: 1030799-93-9
    CAS Registry Number: 128276-03-9
    Formula: C15H27N O4     CA Index Name: Decanoic acid, 2-(2-oxo-3-oxazolidinyl)ethyl ester
U.S. Pat. No. 7,105,646 B2 (Sun Chemical Corporation) describes mono-and bis-azo hydrazone compounds that comprise a pyrrolinone ring for use as pigments.
Coatings, inks and adhesives based on acrylate functional raw materials can be cured in a curing process via a free radical polymerization mechanism. Most often this process is started by irradiation with actinic radiation, such as UV (ultraviolet) light, with photoinitiators present in the formulation to absorb the radiation and generate the free radical initiating species. Alternatively, the process can be initiated by irradiation with electron beam (EB) radiation. The curing process is well known to be inhibited by atmospheric oxygen such that control measures are required to reduce the effect of the oxygen inhibition and allow good curing, particularly at the surface. One method is to use a nitrogen blanket, but this is technically complex and expensive. The more usual approach is to use a blend of photoinitiator types and amine synergists in the formulation.
To those skilled in the art it is well known that free radical photoinitiators fall into two categories; cleavage and hydrogen abstraction types. When in an excited state following irradiation, cleavage photoinitiators undergo homolytic scission to form two radical fractions. Typical cleavage photoinitiators include aryl ketone and phosphine oxide photoinitiators. Cleavage photoinitiators are generally speaking more reactive, but give poorer surface curing because of oxygen inhibition, particularly in the case of phosphine oxide-type cleavage photoinitiators. Hydrogen abstraction photoinitiators typically extract a hydrogen atom from a donor molecule such as an amine synergist to form an inactive radical and a donor radical that is capable of initiating radical reactions. Typical hydrogen abstraction photoinitiators include benzophenones and thioxanthones that form stabilized inactive radicals on hydrogen abstraction. Hydrogen abstraction types only function effectively in the presence of hydrogen donors, such as amine synergists, but this mechanism makes them particularly good at combating oxygen inhibition at the surface.
Phosphine oxide-type cleavage photoinitiators are particularly suited to use in energy-curable compositions that are cured using UV radiation generated by an LED (light emitting diode) source as they absorb, and are excited by, light in the frequency range emitted by LEDs. Phosphine oxide-type cleavage photoinitiators are also particularly suited for use in clear coating and white ink compositions as they typically do not discolour the cured composition and are “non-yellowing”.